


Hold The Line

by mannybothans



Category: Supernatural
Genre: Anal Fingering, Apocalypse world, Archangels are dicks, But more smut, Cunnilingus, Dirty Talk, F/M, Jack does his best, Mild Angst, Mild Fluff, Penis In Vagina Sex, Porn with Feelings, Porn with some plot, Post-Season/Series 13, Pre-Season/Series 14, Reader Insert, Season 13 spoilers, Semi-Public Sex, Semi-Voyeurism, Sharing a Bed, Smut, Spoilers, The Plot Thickens, Vaginal Fingering, a dash of fluff, but so does the porn, but their other songs are also great, coming on command, not that africa isn't a banger, open-ended story, please use condoms, smutty smut smut, toto has more than just one song, uh, unprotected sex
Language: English
Status: Completed
Published: 2019-01-31
Updated: 2019-03-07
Packaged: 2019-10-19 18:01:23
Rating: Explicit
Warnings: Major Character Death
Chapters: 3
Words: 15,216
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17606219
Author URL: https://archiveofourown.org/users/mannybothans/pseuds/mannybothans
Summary: Two years after joining Team Free Will, your entire world has been turned upside down. There's been a line none of you have crossed, but with Dean gone, will you and Sam continue holding the line?





	1. Chapter 1

Two years after Sam and Dean had welcomed you to Team Free Will, the three of you promised each other that you’d enter and leave Apocalypse World together and alive.

But when Sam’s life was literally drained in front of you, it took Castiel to drag both you and Dean out of the tunnel. The vision of Sam being dragged away by vampires as your screams filled your own ears haunted you even as the bleak excuse for daylight nearly blinded you. Dean had gotten instantly angry and refused to acknowledge your wailing for several long moments until he finally picked you up off your knees and forced you to move forward.

When your minus-one group got to “safety,” Dean yanked you aside and told you to pull yourself together. You were a leader and he needed you, now that Sam was gone. It was just the two of you. You nodded quickly, wiped your face, and numbly accepted the responsibility he gave you. When you’d calmed down, Dean embraced you and let out a shuddering, ragged breath. You squeezed him tightly, as if you could absorb him into your own body and therefore never lose him. When the two of you stepped away from each other, you both wore brave faces and swore that you were ready to face whatever else came at you. From then on, it was only about the survivors making it safely over to your world.

“Hey, look, before we rally the troops,” Dean spoke up as you were about to turn heel and leave. You paused and watched as his Adam’s apple bob as he swallowed nervously. “I just wanna say, y’know, that you’re family. I love you.”

“Right. I love you, too, Dean,” you replied and gave his hand a light squeeze.

He looked down and dragged his other hand down his face the way he did when he was tired or exasperated. “Fuck it,” he murmured and pulled you back to him, locking lips in a kiss that caught you mostly off-guard. While the majority of your brain was screaming _FUCK YEAH_ , there was a small bit wondering why he decided to do that just then. Despite the mental conflict, you moaned softly into his mouth as he cupped your jaw in his hands and continued kissing you. It was deep, cathartic, sensual, and made you weak in the knees.

A moment later and several moments too soon, Castiel’s voice brought everything to a screeching halt as he called out to Dean. You weren’t sure if Castiel could see it, but Dean’s reluctance to pull away almost broke your heart. He locked eyes with you before he stroked his thumb across your cheek and left to follow Cas.

_Wellp._ You’d be having a seriously awkward conversation with Dean later; that was for damn sure. His eyes had said things he’d never have the courage to say out loud unless you confronted him.

A commotion nearby brought you out of your head and you rounded the corner to see Dean and Sam hugging – with not a scratch on Sam.

“Sam?” You choked out in disbelief. Your knees threatened to buckle and your head felt like it was floating fifteen feet above your body.

“Heya, Y/N,” he said softly when he parted from his brother. Then, you flung yourself into his arms and he held you for what seemed like an eternity. He was really alive, again.

After that, it seemed like it was only seconds later that Sam was torn from the bunker with Lucifer and Jack, and Dean didn’t hesitate to follow with Michael co-piloting.

When Sam returned with Castiel and Jack, you nearly broke. Before you could even ask, Sam’s face told you everything you needed to know and you sank to your knees, filled with utter despair once more. You knew – you KNEW back there after losing Sam that you should’ve protected Dean. That if you’d had the ability to take his place, you would have. Broken hearted and filled with anguish, you retreated wordlessly to your room.

Jack was the first one to come by your room and assure you that Dean would be found – alive and well.

“Jack?”

“Hm?”

“You still suck at lying,” you mumbled, though you were grateful that he’d taken the time to come see you. Not even Sam had stopped in to check on you. You knew he was hurting, too, and desperate to get Dean back above all else. You weren’t a priority for Sam.

“Yeah, I know,” he sighed and you couldn’t help but grin a little bit. “But you know Sam’s not going to give up until he’s found. _We_ will find him.”

“Thanks, Jack,” you said and he gave you a small smile and left you alone. You pulled your pillow tighter against your chest and brushed your fingertips across your lips, remembering how Dean’s mouth felt against yours, how he tasted, and how olivine his eyes were when he silently told you he’d meant everything he just did.

Sleep came to you, but didn’t last long. The nightmares were awful. Instead of Sam dying in that tunnel, it was you and the brothers watched without emotion as your blood sprayed into the darkness. When Lucifer found your body, he dragged it to hell instead of reviving you and you woke screaming into the dark of your room, sweating, and sobbing.

“Y/N!” Sam’s voice called out as he threw your door open. “Y/N! Are you okay?! What’s wrong?” You heard the click of the hammer on his gun pull back and you bit back a choked sob.

“Just a nightmare, Sam,” you answered after a moment. “Sorry if I scared you.”

“It’s okay,” he replied, disengaging his gun and lowering it. In the light from the hallway, you could see the outline of his bare shoulders and arms. He’d been in bed, too.

The emotions from the terrors your mind had conjured were exacerbated by the knowledge that you’d scared Sam shitless enough to come running with a loaded gun and your body shook with another sob.

“Hey, hey hey hey,” Sam said quietly as he padded over to your bed. “Hey, it’s gonna be okay. None of that was real, right?”

You nodded, sitting up and hugging your knees to your chest. You were a grown adult, a hunter, and practically a Winchester, so you had to get a grip. “Just felt too real.”

“Wanna talk about it?” Sam asked, sitting on the edge of your bed. You shook your head and wiped your face. “Okay. Want me to stay for awhile?” You nodded and Sam scooted up to sit next to you, drawing his knees up and setting the gun on the night stand. He was warm; you put your head on his shoulder and the two of you sat in comfortable silence.

After awhile, your eyes closed and you fell back asleep. Sam didn’t want to wake you, so he settled in and got as comfortable as possible and before he could stop it, he’d fallen asleep, too.

When you woke up a little while later, he was still there. Except the two of you had rearranged yourselves so you were lying down, him pressed protectively against your back with one strong arm draped around your middle and the other stretched out under your pillow. It wasn’t the first time you’d shared a bed with Sam, but it was the first time you’d ever woken up with him spooning you. Feeling much more rested, you reached for your phone and checked the time. It was four in the morning and in just a couple of hours, the bunker would start to come alive with people waking up and getting into their new daily routine. Your door was still cracked open, letting in a sliver of warm light from the still-quiet hall.

“Mm, sorry,” Sam murmured against your neck and he moved his arm from around you. “Didn’t mean to fall asleep.”

“It happens.”

“Time is it?” His voice was heavy with sleep and you realized there were only a handful of times the two of you had spoken while on the edge of wakefulness. And never while he was so close to you, physically. There was a new level of intimacy in the situation that made your pulse quicken.

“Four-ish,” you yawned.

Sam hummed in reply. “Guess I should go,”

“You can stay,” you interrupted. “It’s nice. I feel safe. And you’re warm.” You pushed back against him to make your point and Sam’s entire body stiffened at the movement. It only took a moment for you to understand why. “S-sorry,” you said, sheepishly.

“It, uh, it’s not your fault,” Sam cleared his throat. “I mean, uh, don’t – don’t worry about it.”

You pursed your lips and squeezed your eyes shut, trying desperately not to move any muscle in your body. Mind racing, you tried to come up with an idea that would slice through the awkwardness that settled over the both of you. For whatever reason, your sleep-addled brain thought if Sam grabbed your boob, you’d be even. You felt his hard-on, so he should get to cop a feel, right?

“Wh-what are you doing?” Sam asked, a tinge of panic in his voice when you grabbed his hand and placed it right on your breast.

“I, I just, I thought since I felt your erection, if you grabbed a tit, we could just laugh it all off and move on?!”

“I, Y/N, that’s, I mean,” he huffed, leaving his hand cupped around your breast but made no move to touch you aside from what you were basically forcing him to do. “It’s a nice thought? But, I, I don’t think it’s helping.”

“Right, god, sorry, I’m so sorry,” you let go of his hand and covered your face, despite the fact he probably couldn’t see you from how he was positioned behind you. The warmth from Sam’s hand didn’t dissipate at all, because he never moved it. Instead, he gently squeezed.

“Is that okay?” He asked after a moment when you didn’t move or say anything.

“Uh, yeah, of course.” You forced a grin, hoping he could hear it in your voice. Truth was, it was kind of turning you on and you didn’t really want him to stop. “We good, now?”

“We can be,” he replied, giving your breast another gentle squeeze. “But I should probably tell you – I really like this.” For a split second, you heard Dean’s voice instead of Sam’s and your heart leapt into your throat. It had to be because Sam’s voice was so low, so full of sleep, still, that it reminded you of Dean. As thoughts of Dean filled your mind, Sam gently rolled your nipple between his fingers and you bit back a needy moan; your hips, however, pushed back into his again as your back arched into his touch. Sam hissed through his teeth and it brought you back to reality. “Y/N,” he said and it sounded like a warning more than anything.

“Hmm?” You sighed, trying to sound as casual as possible.

Sam went quiet and though he still cupped your breast, he no longer squeezed it or pinched your nipple. A sense of unease settled over you and you wondered if he was having an internal debate on whether or not to cross that line you’d all drawn years ago when you joined Team Free Will. You were almost certain that the brothers had agreed neither one would sleep with you and that you’d all just be one small, happy family to keep the business running. And yet here you were, Sam’s hard cock pressing into your ass and his hand on your breast, ready to possibly erase that line with one phrase, a couple words, or an action.

You’d done mental gymnastics to avoid imagining either Winchester as a sex partner for yourself. It meant imagining them fucking some faceless body while you got off. Flirting was rampant between the three of you, but it was always harmless and led to nothing, not even a hint of anything more, until Dean had kissed you and made that promise with his eyes.

Steadying your breathing, you swallowed the uncertainty. Life was short for a hunter, too short in most cases, and tomorrow was never promised. Even if it was, it only took a split second to get ripped right out of your hands. You turned towards Sam and his eyes opened, locking on yours. Before you could blink, his lips were on yours and your fingers were twined in his hair.

There. Line erased.

Sam’s kiss was nothing like Dean’s – Dean’s had been emotional, full, and slow. Sam’s was needy and filled with longing. He kissed you like he’d been waiting his entire life to do so and you wondered how much sooner this line would have been crossed if anything had happened to Dean earlier. He was eager to taste you; his tongue wasted no time in pushing past your lips and teeth. Because you were facing him, Sam’s hand that had been cupping your breast was now latched firmly on your hip. He pulled you against him, rolled his hips against yours to ensure you could feel every solid inch of him, and drew a long, low moan from you in doing so.

A thought briefly flickered across your mind: Did Sam mean for this to happen when he came to your room earlier that night?

Decidedly, it didn’t matter. Not when he shifted and used his hips and thighs to roll you onto your back, then caged your shoulders with his elbows while his tongue explored every millimeter of your mouth. You were absolute putty in Sam’s hands and you didn’t care about anything else except how he felt above you.

Just when you thought the kissing would never end, Sam slowly broke away and moved his lips to your chin and jaw. He hadn’t shaved in days and the thicker-than-usual beard stubble tickled your neck and cheek. A soft whimper escaped your lips when he flicked his tongue into your ear and then bit your ear lobe. Sam didn’t make a noise, didn’t utter a single syllable, as he wedged his knee between your thighs. He didn’t have to; you ground yourself against him, unaware how much you needed the friction until you were desperate for more. He finally slipped a hand under your shirt and grasped your breast again, causing you to gasp and arch into his touch. His rough fingertips rolled your hardened nipple back and forth, gently pulling and tugging as if to see what kind of noises you’d make.

“Sam, please, I,” you panted, feeling the dampness between your legs grow as you rolled your hips, grinding harder against his thigh.

He rumbled in response and pushed your shirt up, exposing your tummy but not your breasts, then sat back on his shins as his long fingers grasped the waistband of your sweatpants and tugged them off your hips. You watched as his tongue darted out to moisten his bottom lip while he gazed at your pubic mound. Sam removed his knee from between your thighs so he could pull your sweats down and fully expose your pussy. He cupped your mound as if in awe; if he could have seen your face more clearly, he would’ve seen your cheeks turn bright pink when he said, “Christ, you’re so wet. I’ve wanted this for so long.” Sam pulled his hand away and pushed your thighs open a bit more, just taking all of you in, admiring your cunt as he teased your folds with his thumb.

“Shit, Sam,” you breathed, trying not to beg for it. You hadn’t gotten laid in such a long time, but you definitely didn’t want to rush _this_.

“Is this for me?” He asked huskily, pushing his thumb into your drenched folds and smearing your slick around.

“Yes,” you moaned.

Another groan rumbled out of him and goose bumps rose on your flesh. He swirled his thumb through your folds again and then found your entrance and pushed into it. Your opening gave way for him and the both of you moaned. “Fuck, Y/N, so pretty.” You exhaled sharply and he withdrew his thumb, replacing it with his middle and forefingers almost immediately. “So tight,” he murmured. “S’been awhile?”

“Too fucking long, Sam,” you whined. “Need it. Need you, now, please, for fuck’s sake,” the words tumbled out of you as you gave up trying not to beg for it.

Sam fucked you with his fingers, curling them upwards against your g-spot and you nearly wailed before you could cover your mouth with your hands. “That’s right,” Sam grunted. “Gonna make you come so hard.” He lowered himself onto you again, slamming his fingers into your eager cunt over and over again while he watched your face twist with pleasure. “Can’t wait to fuck you. Gonna make you feel so good,” he half-whispered into your ear and you shuddered, bucking against his hand.

“Oh my god,” you panted, trying to stay quiet since your door was still slightly ajar. He cut you off, slanting his mouth against yours in another deep, passionate kiss. You clung to him and forgot how to breathe as he coaxed you to the edge of bliss.

“Come for me, baby,” he rasped when he finally pulled away from your kiss-swollen lips.

A whimpering keen was forced from your lungs when you realized he was capable of making you come on demand and you covered your mouth as your body arched against him, pleasure flooding every sense and nerve ending. It was the hardest you could remember coming in a very, very long time. He gradually slowed his hand but waited until your pussy was done pulsing and spasming around his digits before he removed them. You uncovered your mouth to tell him to fuck you; his fingers, covered in your slick, filled your mouth before you could even begin to speak. Your tongue cleaned his fingers eagerly. You always thought you tasted pretty good, but on Sam’s fingers? You tasted heavenly. He watched rapturously and then kissed you before you could swallow, stealing the taste of you from your own mouth.

You reached up and buried your fingers into his hair, moaned into his mouth, and lifted your hips to signal you wanted him _now_. Sam got the hint and he quickly shed his own sweatpants, then settled between your spread legs. You could feel the heft of his cock settle between your legs, but you hadn’t seen it.

“Ready?” He asked, which you found thoughtful and sweet.

“Fuck me, Sam,” you answered.

He pushed his throbbing cock into you and your head snapped back as he split you open. You _thought_ you were ready but nothing could have prepared you for his width. A surprised gasp left you and he stilled.

“You alright?”

“Don’t stop,” you groaned. “Please don’t fucking stop.”

With a huff – whether amused or concerned, you weren’t sure – Sam finished pushing into you and then slowly withdrew. He was starting off slow to get you used to his size but honestly, you just wanted him to ram you until the bed broke. He leaned down and kissed you, gently this time, no tongue, as if checking on you. You moaned quietly to encourage him and his hips started moving faster, little by little. Soon, you were clinging to his shoulders, one leg hooked around his hip as he pounded into you. Quiet, punctuated gasps and moans filled your room and Sam happily swallowed the loudest noises he drew from you.

“God, you feel good,” he whispered into your ear. “So much better than I imagined.”

“You, nnh, how long, Sam?”

“Too long,” he grunted almost angrily. “Tried not to, hhnh, tried not to think about fucking you – didn’t work.”

The thought of Sam jerking off while thinking of you – or even trying not to think of you – made your toes curl.

“Same, fucking Christ, same,” you panted and he rammed deep into you, withdrew nearly all the way, and rammed in again. You bit back a scream and he bit into the side of your neck.

“Yeah? You thought about this cock? Fucking you, filling you, making you scream?” Okay, if he was going to talk like _that_ , you were going to actually die. Before you could even think of how to answer, his large hands were on your waist and he was deftly rolling onto his back, pulling you on top of him. You straddled his hips and started riding him without missing a beat. He shoved your shirt up over your breasts and you yanked it off, tossing it to the floor somewhere beside the bed. Instantly, his hands covered your bouncing tits and squeezed them firmly. Your hands covered his and he squeezed harder.

“You like this, Sam? Like me riding your cock?” You didn’t have time to wonder where that came from.

“Shit, yeah,” he moaned and then dropped his hands to your hips. He shifted under you, planted his feet on your mattress and bent his knees; you canted forward and grasped his shoulders as he pounded up into you mercilessly. You wailed into the side of his neck, hoping between him and the pillow, it would be muffled enough to not bring unwanted attention to your early-morning activities. “Fuck, ‘m gonna come, baby,” he panted.

“Wait, please, fuck, I’m so close,” you pleaded. Sam immediately shoved a hand between your pelvises and his fingertips easily found your swollen clit. He rubbed it quickly, using just the right amount of pressure while his hips pistoned in and out of your sopping, stretched cunt. He groaned when you tightened around him and you begged him to keep going. A slight change in pressure on your clit had you seeing stars as you came on his cock; the breath was punched out of your lungs in a long, low moan while your entire body shook with release.

Sam took two sharp breaths and then pulled your hips off of him as he came all over his abdomen with a shuddering, restrained groan. You collapsed next to him, reached over to your tissue box, and handed him several tissues to clean up while you both caught your breath.

That was the most mind-blowing sex you could remember having and it made you giggle softly.

“Something funny?” Sam asked, discarding the tissues once he was done mopping himself up.

“No, that was just, wow,” you said, grinning at him as he turned onto his side, propping up on an elbow.

“Yeah, it was,” he agreed and leaned in to gently kiss you. He reached over you, grabbed your phone, and checked the time. “S’only five, we could still grab another hour of sleep before everyone starts getting up,” he suggested.

“Sounds good,” you replied and pulled your covers up over the both of you. Sam pulled you to his side and you rested your head on his chest. “This alright?”

“Mmm,” Sam confirmed.

A second later, there came a quick knock on the door and it swung  the rest of the way open, drenching your room in light from the hall so you couldn’t see who was standing in the doorway. A colorful string of curses left both you and Sam at the same time.

“I figured I’d wait until you were done,” Jack announced. “Sorry, but, we might have a lead on Michael’s location. Sam, you said to get you, no matter,”

“I know what I said!” Sam bellowed. “I’ll be out in a minute!”

Jack left in a hurry, leaving the door wide open.

“Close the goddamn door!” You and Sam shouted after him. Jack rushed back and closed the door before darting away once more.

You took a deep breath and buried your face in Sam’s shoulder. “So much for that,” you drawled out.

“I’ll make sure he doesn’t say anything,” Sam assured.

“You think he heard? I mean we were kinda quiet?”

“Dunno,” Sam answered as he swung his legs out of bed. You sat up and turned on the lamp beside the bed. Clothes were strewn everywhere. You picked up Sam’s pants, tossed them to him, then found your own and began dressing. He pulled his pants on and strode over to you. “Meet you in the library in a few? Maybe we can shower later.”

“Together?”

“Definitely together,” he said with a small, wry grin, just before he kissed you. “And hopefully without an audience. Unless you’re into that kind of thing?”

You laughed and playfully slapped Sam’s arm. “Fuck off, Winchester.”

“That’s the idea,” he teased and kissed you again. “See you in a minute.”

“Yeah,” you agreed. He left your room quietly after taking his gun off the nightstand, like he was sneaking home after curfew. Your heart leapt at the news of Michael and now it was sinking into your stomach. You loved Dean, you really did, and you missed him terribly and wanted nothing more than to have him back, to hug him and feel him against you once more. You’d give anything to endure one of his angry outbursts or just to hear him and Sam argue over the stupidest shit again. And yet, you’d just slept with Sam. And it was _really fucking good_. “Fuck,” you sighed as you ran your hands through your sex-mussed hair. “Fuck, fuck, fuck.”

And that, you realized, was why there was a line to begin with.


	2. Chapter Two

**Summary for the Chapter:**

> Dean returns and you're left wondering if there's even a line to hold, anymore.

The Next Week

“Sam!” You gasped his name as he braced you against the wall, his mouth sucking and licking the side of your neck while his hands held your thighs and his cock thrust deep into your core. The hallway rendezvous had started innocuous enough, but soon Sam’s mouth had claimed yours and not long after, his fingers were opening you up, readying your cunt for him. It was the easiest way to let off steam from the false leads on Michael piling in day after day.

“Ssh,” he replied. “Don’t want everyone to hear.”

“We could just go to a room!” You hissed back. Sam responded by thrusting harder up in to you and you threw your head back, squeezing your eyes shut as a loud moan threatened to escape from your throat.

“Too late,” he muttered into your neck. “Fuck, baby, you feel so good.” You reached up and grabbed fistfuls of his hair, causing him to groan and hiss quietly but the slap of his hips against yours only got faster. He wedged a hand between your bodies and his fingertip immediately found your swollen clit.

“Sam, please,” you panted. “I can’t come again, not without causing a scee-heeene, fuck!”

He wasn’t going to give up until you were coming on his cock and you knew it, and he knew that you knew it, and you knew that he knew that you knew it.

“Yes, you can, baby. I know you can. Come for me. Just one more time,” he growled into your ear and it gave you gooseflesh all down your left side. “Need to feel you,” he added after licking the shell of your ear.

Your eyes screwed shut again and you held your breath as Sam’s fingers and cock coaxed you over the edge. You let go of his hair to cover your mouth as you wailed silently in the throes of an intense orgasm; he fucked you through it, his hold on your thigh almost bruising. As soon as you finished, he was following you over that edge into bliss, releasing into a condom you’d produced and made him put on when it was clear that he was going to fuck you. Sam panted to catch his breath and it was hot and damp on your neck.

“Shit,” you exhaled, letting your rubbery-feeling legs unwind from his hips even as he carefully pulled out of you.

Sam tucked himself into his pants with a grin on his face. “We should do this more often.”

“We should?” You narrowed your eyes and kept your voice low as you pulled your panties and jeans back up, almost shivering at the cold wet spot against your still-warm sex.

“Maybe not in the hallway, but, yeah, we should do this more often.” He leaned down to peck your lips and you were going to return the kiss when footsteps around the corner forced Sam to jump back from you even as he continued fixing his clothes. “So, um, good job on that lore research today. You’ve been a huge help, as always,” he said loudly right as two of the new recruits came around the corner and quickened their pace as they giggled past you.

“Sam? Is that you?” It was Bobby’s voice. After all the stories you’d heard about Sam and Dean’s Bobby, it still felt like you were interacting with a ghost each time.

Sam cleared his throat and shot you a quick, apologetic grin. “Yeah, Bobby, it’s me.”

“Is Y/N with you?”

“Uh, yeah,” Sam began.

“Yeah, I’m here,” you called out as Bobby came into view.

“God, where the hell’ve you idjits been? C’mon, another lead got called in half an hour ago.” Bobby’s eyes took in your disheveled appearances and you couldn’t help the blush that spread from your mouth-bruised neck to your cheeks. “Jack’s too scared to look for you, so I’ve been wanderin’ around for the last twenty minutes lookin’ for ya,” he explained gruffly.

Your eyes flicked up to Sam’s right as he pursed his lips and Jesus, if Bobby didn’t know what you two had been up to by now, he surely saw it in that silent exchange.

“Really? In the hallway? Kids,” he rolled his eyes and grumbled, turning back the way he came. “You better pray I don’t get lost in here and die, or else I’ll haunt your stupid asses for the next eight millennia!”

You waited until Bobby was well out of earshot before you let go of the breath you’d been holding. “Jesus, Sam,” you sighed. “How many more people are going to find out?? We can’t, we _shouldn’t_ ,”

“Hey, who cares? We’re adults.”

 _What if Dean finds out?_ You thought, then squashed it. It was looking more and more like Dean wouldn’t be coming home anytime soon. As if reading your mind, Sam wrapped his arms around your shoulders and pulled you into his chest.

“As soon as we find Dean, I’ll tell him. That way it’s just… out in the open. Okay?”

“Are you sure?”

“We could just not tell him, I guess,” Sam shrugged as he smoothed your hair into place.

“Yeah, because that works so well in every other instance,” you drawled, the sarcasm nearly dripping from your words.

Sam sighed and you stepped back from his embrace. “We’ll cross that bridge when we come to it.”

“Right.”

“C’mon, before Bobby gets lost,” Sam grinned and reached for your hand to take. You wove your fingers through his, locking your palms together, and let him lead the way back to the main areas of the bunker. You took your hand back before anybody else saw you two together, though, and Sam frowned a little bit.

The lead on Dean turned out to be yet one more dead-end and Sam called it a night before another lead could get anyone’s hopes up. You retreated to your own room and Sam went to his; but, like clockwork, at 5am Sam slipped into your bed and between your legs.

 

Four Weeks Later

Sam had been gone for over a day when you decided to call him to see how it was going and if the lead had panned out.

“Sam’s phone,” came an eerily familiar voice. Your voice stuck in your throat and you fumbled for the nearest chair to fall into. “Y/N? You there?”

“D-Dean?”

“The one and only,” he replied and you could hear his little smirk. “So, you and Sammy, huh?”

“Wh-what? I,”

“He told me everything,” Dean said casually.

You had no idea what to say, so you just sat and got angry with Sam. For once, he didn’t keep a secret from Dean.

“You there, sweetheart?”

“Y-yeah,”

“S’good to hear your voice again,” Dean said lowly, almost sounding seductive. “We’ll be back later this evening.”

“Okay,” you managed to croak out.

“Okay. Talk soon,” he said and you could practically hear the little smirk on his face before he hung up.

 “Oh my god,” you gasped, holding your phone so tightly your knuckles whitened. Jack saw the look on your face and his brow knit in concern. “S-Sam. He found Dean. They’re, they’re coming home,” you said slowly, as if each word weighed a ton.

“Attention, everyone,” Jack said, raising his voice over the quieting din of the new bunker residents. “Dean Winchester is alive and safe. He’s on his way home.”

A small cheer went up from those around you and you thought you might faint if you tried to stand up. Sam was on his way home with an archangel-free Dean. A Dean who knew that his brother had been hooking up with you while he was away. A Dean who didn’t sound one bit angry or bitter about any of that, just… _amused_. You supposed Dean really didn’t harbor feelings for you, hence the lack of anger or bitterness in his voice. That was an easy pill to swallow – he’d never had feelings for you, anyway.

The rest of the day went by in a haze as you debated whether or not it was futile to try to look nice for Dean’s return. The fact he didn’t care about you and Sam stung a little bit, so you wanted to look nicer than usual. Obviously, you didn’t want to look like you were trying super hard since Dean was bound to not even notice.

While lost in thought, a dark green shirt caught your eye; the sleeve was peeking out from between some other stuff hanging up. The last time you’d worn it, Dean had given you a genuine compliment. It was, of course, met with a silly deflection, but Dean just winked in response. _Right then,_ you thought, _don’t over-think this_. You pulled out the shirt in question and a clean pair of jeans; a bra and panty set that wasn’t _too_ sexy, but sexy enough to give you a little confidence boost rounded it all out. Then, you framed your face with lashes, brows, and lips – subtle and enhancing.

Before you knew it, it was 8:00PM and the Winchesters were due back any minute. It took a couple of shots of whiskey to calm your nerves in the minutes leading up to their arrival. Except they didn’t show up at the designated time. A text from Sam around 9:30PM told you they wouldn’t be getting in until much later, probably around 11:00PM. You wondered what had set them back so far, but decided it didn’t matter in the long run.

You were in the kitchen nursing a glass of whiskey when Sam finally texted and said they were back.

The metal door at the top of the stairs in the War Room slammed and it took effort to not run in there, especially when you realized you weren’t the only one awaiting the brothers’ return. Several of the new recruits had gathered once word had gotten around that the Winchesters, their saviors, would be back. Boots clomped down the stairs as your eyes tried to focus through the inevitable tears that formed in the corners of your eyes. The whiskey in your system did nothing to help quiet the pounding of blood in your ears as Sam and then Dean descended the stairs.

Dean’s eyes found you almost immediately, even as Sam’s scanned the room while he nodded reassuringly at the new residents. The several others who had crowded into the room started a small applause and Dean lowered his head in a somewhat bashful manner. Sam smiled, weaving through the crowd in your general direction as the brothers got clapped on their shoulders and arms for a job well-done. Rounds of thanks and gratitude filled the air but you were left speechless as Sam and Dean drew closer. Finally, they stopped in front of you, Sam still smiling, although he looked a bit nervous. Dean’s eyes sparkled as his lips turned up into a small smirk, as if he knew you’d been waiting for him.

“You’re back,” you breathed out in relief, trying to keep the moisture in your eyes from escaping with each blink.

“I am,” he replied in that gravelly voice that stirred dormant feelings deep within you. He crooked his arms out just enough to invite you to hug him. And you stepped forward, letting your body collide with his as your arms wrapped around his broad shoulders and his closed tightly around your waist, pulling you to him even as he braced himself against the force of your hug. He was warm and solid under your hands and against your chest. The entire room fell away as Dean’s essence surrounded you.

“Welcome home, Dean,” you managed to choke out as you pressed your face into his neck.

“Good to be back, sweetheart,” he replied just as quietly and gave you a firm squeeze before he stepped back and loosened the embrace. His eyes briefly searched your face and you wondered what he saw there, even as your mouth turned up into a smile that you knew didn’t reach your eyes.

“Are you guys hungry? I can heat something up,” you said, hoping to spend time with just the two of them and catch up on some of what had happened in more detail than just: _Sam Find Dean. Dean Not Meatsuit. Sam Bring Dean Home._

“I’m beat, actually,” Dean said and scratched the back of his neck. “Long few weeks.”

“Right,” you nodded. “It is late. I suppose we can all talk tomorrow.”

“Yeah,” Dean nodded back. “Night, Sammy. Night, Y/N.” He clapped Sam on the shoulder and went for a one-armed hug with you. It was better than nothing. Still, something seemed a little off about Dean – maybe it was really just the exhaustion or recovery period from being worn around by Michael.

Sam kissed your forehead before he decided to turn in, as well. You sat on the table and finished your whiskey, then headed to your own bunk for the night.

**

You woke suddenly at 6:00AM and rolled over to find your bed empty. No Sam. It was strange, but you figured he was probably beyond tired from the hunt and the drive. So, what had woken you up? Sitting up, you rubbed your eyes and then saw a shadow shift outside your door. At first, you thought it was just someone walking by. But the shadow didn’t disappear and there were no footsteps fading away down the corridor. Someone was outside your room.

“Sam?” You called quietly. He usually didn’t linger outside your room like this and something told you it wasn’t Sam. You flicked on the lamp at your bedside. It cast the faintest golden glow on your nightstand; the rest of your room was still doused in long, dark shadows. Quietly, you slipped out of bed and tip-toed to the door; you held your breath to see if you could hear anything on the other side.

You slowly turned the knob and pulled the door open. The hall lights dimmed during the night, but it was still much brighter than your room. Through the crack in the door, you saw Dean’s retreating form, heading back down the hall towards his room.

“Dean?” You called, softly. “Everything okay?”

He stopped and turned, scratching the back of his head. “Uh, yeah, I just… I was uh, takin’ a walk.”

“I saw your shadow,” you stated flatly. “Did you need something?” He was dressed a plain tee-shirt and a pair of sweatpants you didn’t recall ever seeing before.

Dean made his way back down towards your room, checking down the corridor for any others that might be up and around. “Uh, not really, I guess. Sorry I woke you.” A long pause of silence, which you didn’t dare break because you knew eventually Dean would get to the point. “Is, is Sam in there? With you?”

“No, Dean, he’s not,” you pushed the door open so Dean could see your messy bed, empty of any other bodies. “Is that why you came here? To see if Sam was in my room?”

Dean’s jaw flapped as he tried to think of what to say that wouldn’t sound downright creepy or weird. “N-no?” Another drawn out moment of thick silence between you two. “Maybe?”

“Don’t make this weird, Dean,” you sighed. “Sam and I,” you faltered, wondering why you felt the need to explain yourself to him. “We, I mean, it just kinda happened, y’know? You’d disappeared and we had no idea if you were ever coming back. We had no idea if we’d ever find you again. That day, in Apocalypse World, when you kissed me,” Dean huffed and put his hands on his hips, then stared down at the floor, as if he were insulted. “When _we kissed_ , we thought Sam was gone forever. I think we both realized that no matter how good we are at what we do, this life? It’s short.”

“I know,” Dean nodded, lifting his head just a bit too briefly make eye contact. He rubbed a hand down his stubbly cheeks. “Boy, do I know.”

“Then you understand. With you being gone,” you trailed off, letting Dean fill in the blanks. He was smart enough to work it out, and you were almost positive he already had.

“Right. It’s just one of those things; you realize tomorrow’s not guaranteed and why waste a good thing?” He shrugged as if he hadn’t just said you were a _good thing_.

“Yeah,” you replied, leaning against your doorframe, now.

“R-remember when Billie paid me a visit last year?” Dean asked, suddenly. You nodded slowly, wondering what he was getting at. Dean bit his lower lip for a moment. “She said something about you that I never mentioned.”

“Which is?”

“That your fate was sealed. That if Sam and I kept messing with rifts, we could lose you. I didn’t, y’know, I don’t believe in that crap, never have, but she, ah, she was convincing. Before we all went into Apocalypse World, I told Sam I had a feeling something bad was going to happen to you. We agreed we wouldn’t let it. That’s why he, in the tunnel, when he...”

“Dean, that’s ridiculous. None of our fates are _sealed_. We’re Team Free Will, remember? We make our own fates. Besides, why didn’t Sam tell me any of this while you were gone?” You asked in a challenging voice, unsure whether or not to believe Dean.

“He promised not to. I promised, too.”

“But here you are,” you said slowly, trying to make sense of what Dean was saying. Suddenly, he believed in fate? Who was this man standing in front of you, preaching the ways of the universe like a true believer? “Breaking promises.”

Dean’s head snapped up at that and his gaze was intense. “I’m telling you because tomorrow’s not promised. I was just ridden by an archangel for weeks on end and, and, and all I could think about when I wasn’t fighting him, was you and getting back to you, to the bunker, to this life. I didn’t know if you were safe. And Michael knows – he knows about you. He knows what Billie said about you, he knows everything about you that I do,” he paused, letting his stare confirm that yes, Michael did know what kissing you was like, thanks to being inside Dean’s body and mind. Dean sighed and his eyes darted down the hallway once more at the sound of a door closing.

“You don’t think he’d use me, do you? To get to you?”

“It’s a possibility. I thought I’d wake up one day and find you lying dead on the floor in front of me, as a cruel joke. I was so scared Michael would make me,” he swallowed thickly and resumed staring at the floor, unable to finish his thought.

This was why Dean never let anyone in – this was the exact reason. Because it only took one dick archangel to get into his mind and reveal all of his weaknesses. And now you were one of those weaknesses – even if Dean didn’t have _real_ feelings for you, just the fact he had a memory of a kiss with you might be enough for Michael. But what if it wasn’t?

“Why? Well, I mean, it’s not like you have feelings for me. I know I’m part of the team, but what’s to say Michael would come after me before he goes after Sam or even Jack, first? They’re way more important,” you trailed off when Dean’s eyes shifted to the side and he didn’t look at you as you spoke. “Right? Dean?”

“Right, yeah, sure,” he shrugged and you knew he’d closed himself off at some point.

“Let’s just find him before he finds us,” you suggested, as if it were really that simple.

Dean nodded in agreement but didn’t move otherwise.

“Was there something else?” You asked carefully, not sure if you’d like the answer or not. Dean looked frustrated, tired, and like he was mad at himself. “I should probably get dressed and see if Sa,”

You were cut off when Dean was suddenly pressed against you, his lips against yours, erasing all thoughts of anything else. His hands cupped your face and your own flew to his wrists, unsure if you wanted to pull his hands away from you or keep them there. Your mind raced and you were about to pull away from him when his tongue flicked against your lips to ask for entrance and, without thinking twice, you opened your mouth to let him in. You had morning breath that tasted like stale whiskey, but Dean didn’t seem to care as his tongue slid against yours in a gentle, almost sweet give-and-take.

Dean used his hips and shoulders to turn you in your doorway; he guided you back into your room and out of such a public, well-lit space as the residents around your room began to wake up. As if he did it all the time, he paused long enough to kick your door shut before he resumed guiding you backwards, unquestionably towards your bed. His hips came into contact with yours again when the back of your knees hit your mattress and you moved your hands to his chest, coming to your senses long enough to nudge him away.

You were almost panting at the intensity of his kiss and how smoothly and easily he’d cornered you in your own room. The look in his eyes wasn’t predatory in the slightest, although you half-expected it. Rather, his eyes were filled with concern and questions he didn’t know how to ask out loud.

“Dean,” you said warily. “What are you doing?”

“I,” he shook his head, his eyes widening in mild panic. “I’m sorry, I just, I had to see if there was anything there. If I’d imagined it all back in Apocalypse World.”

“Imagined? What are you talking about?” You absently wiped your mouth with the back of your hand when Dean had stepped back several inches. He didn’t miss how your eyes flicked nervously to the door.

“I felt something, Y/N, back there. I know we had something. A connection.”

“Dean, we were traumatized. We had just watched Sam die; lost a part of the team,” you were trying to convince yourself, as much as you were trying to convince him, that that’s all it was. “It was grief you felt.”

“So, just now? That wasn’t grief,” he argued, keeping his voice low and quiet. “Sam’s alive. No trauma.”

“Dean, don’t,” you tried, but even you heard the lack of conviction in your voice.

“Tell me you don’t feel anything, Y/N, and I won’t. Tell me you don’t feel anything for me. And I’ll leave you alone, I promise.”

 _I can’t_ , your brain cried out, even as your mouth tried to form the words Dean was asking to hear. “I don’t,” you exhaled shakily, using every ounce of willpower to not burst into tears at the blatant lie.

“I can’t,” you finally managed around a growing lump in your throat.

“You can’t what?”

“I can’t tell you that,” tears threatened your eyes as you watched him suck in a deep breath and hold it for a long moment while he digested the situation. You were almost one hundred per cent sure he wasn’t expecting you to say that.

“Because you _do_ feel something,” Dean said slowly, rolling each word around his mouth and tasting them individually. You could only nod, afraid if you said anything you’d wind up a blubbering mess. His gaze held yours for a long few seconds before you had to look away or else drown in those intensely olivine eyes that held years of pain behind them. As if he were underwater, Dean slowly closed the gap between you and you held your breath when his hands grasped your hips, his hands rough against the ponte knit of your leggings. “I’m going to kiss you, again.” He murmured, searching for something in your eyes. A betrayal or a truth – you weren’t sure which.

“Yes,” you responded. Even as your hands lifted to his neck, his mouth slanted against yours and you parted your lips for his tongue. His pulse points were steady and hot under your palms as your thumbs slid along his sharp jaw while he kissed your breath away once more. Somehow, even with everything else that had happened, Dean’s kiss was still so deeply sensual and emotional that you couldn’t stop the tears from sliding down your cheeks. It felt so good to have him back, alive and safe, that it was overwhelming to feel him against you from mouth to thigh while his tongue slowly explored your mouth. You pushed your tongue against his and he pulled back, letting you into his mouth with a soft groan.

His hands gave your hips a squeeze and then moved up your sides, pushing your tank top up to your ribs and then just under your breasts. Your nipples hardened at the proximity of his hands and the warmth they emitted versus the coolness of your room. Dean sighed into your mouth and then pulled away from the kiss very, very slowly. You slid your hands from the sides of his neck to his broad, muscular shoulders and gave them a light squeeze.

“I want you. I want you right now. I don’t know if we’ll live to see another day, let alone tonight,” Dean murmured against your lips. “I can’t take that chance, not knowing if I’ll ever be with you again.”

“Talk about detrimental FOMO,” you teased lightly, afraid you were going to cry if you didn’t say something silly.

Dean’s lips tugged into a small smirk. “Is that an okay?”

“Dean Winchester, do you really have to ask _anyone_ if they’re okay with you fucking them?”

“Always,” he breathed, dipping his head more to nip at your neck. “Just like I need to know if you’re okay with me taking your shirt off,”

“Yeah,” you sighed as his licks and bites gave you gooseflesh.

“And your pants,” he added after a long, slow lick.

“Mmhmm,” you breathed, feeling the heat between your legs grow exponentially.

“And I need to know if I can touch you where ever I want,” he said lowly, then sucked lightly at the curve where your neck met shoulder.

“Wh-where? Where exactly do you wanna touch me?” You closed your eyes; the dampness between your legs was surely pooling in your panties by now.

“Everywhere,” he answered, then his tongue flicked against the shell of your ear, causing your gooseflesh to actually _hurt_. “I wanna touch your breasts,” he emphasized by nudging the sides of them with his thumbs. “Your cunt,” he pushed his hips into yours and you could feel his unadjusted erection against your upper thigh. “Maybe your ass,” he grinned and shifted to kiss your lips again.

“Is that it? I mean, you just wanna touch me?” You were blatantly teasing him, now. You knew damn well the man wanted to fuck you into your mattress with his throbbing hard-on and it was taking all of your self-restraint to not grab him through his sweatpants. “Am I allowed to touch you?”

“I fucken wish you would,” he groaned against your mouth, grinding his cock against you.

“And if I wanna do more?” You slipped a hand between your bodies and grasped Dean’s thick length over his pants.

“Please do more,” he almost growled, bucking into your hand.

“Fuck, Dean,” you sighed, knowing full-well how wrecked you sounded.

“Uh-huh, that’s the plan,” he countered. “Arms.”

You let go of his cock and lifted your arms so he could peel off your tank top. Once it was off and over your head, tossed unceremoniously to the floor, his hands utterly engulfed your breasts and his mouth covered yours, swallowing the small, needy moans he elicited from you as he touched you.

“Bed,” he added, nudging you backwards between kisses. He followed you as you sat and then scooted towards the middle, laying back, letting him climb on top of you while his hands squeezed and kneaded your breasts. “Pants,” he repeated and you hooked your thumbs into the waistband of your leggings and pushed them and your underwear off in one smooth motion. Dean moved aside to let you safely kick them off and then you were naked under him in the dim golden light of your bedroom. You realized you were holding your breath, so you slowly exhaled as his fingers trailed down your side to your hip and they faltered; you guessed he didn’t realize you just went ahead and took everything off. “Shit,” he swore under his breath. Dean adjusted his actions, moved his hand towards the apex of your thighs and you only knew he was there when his fingertips brushed the short, trimmed curls between your legs. Without being asked, you opened your legs for him and he slid two thick fingers down the center of your folds, gathering the slick there and smearing it further. “So wet,” he observed with a low groan, turning his head to watch his fingers disappear into you.

You gasped when Dean pushed his fingers into your core and aside from your quiet moans, his deep breaths, and the sound your wet cunt being fingered, the room went silent. You closed your eyes again and felt Dean shift above you. Then his lips sought yours, first pressing against the corner of your mouth, then centering on yours. He groaned softly and then pushed his tongue into your mouth at the same pace his fingers were slowly fucking you. You whined into his mouth at the sensations, your brain unable to make sense of anything aside from the utter need to come and the knowledge that Dean Winchester definitely knew how to make that happen.

Dean broke the kiss and shifted downwards, using his free hand to push your breasts up as his lips, teeth, and tongue began working them over. He scraped his teeth across each hardened nipple and basked in all the tiny noises you made for him. His fingers pushed harder into you and his thumb joined in, pushing against your clit with steady pressure as he moved it in slow circles.

“Oh my god,” you gasped, your hips twitching for more.

“God has nothing to do with this,” Dean grinned as his mouth released your nipple with a satisfying _pop_. “Dean, however,” he trailed off as his thumb released your clit and then began flicking it lightly. “Mm, wanna taste you,” he groaned.

“Yep! Yeah, please, yep.”

Then he was between your thighs, his fingers fucking steadily into you as his tongue attacked your clit and you knew he wasn’t going to make you beg for it. All the stories you’d heard, the ones where Dean had an oral fixation, suddenly made so much sense. He lapped relentlessly at your clit and then he withdrew his fingers, leaving you empty and wanting. You reached down and buried your fingers in his short hair, tugging gently as he used his fingers to smear your wetness farther down, over your perineum and around your asshole. You glanced down and his eyes flicked up, meeting your blissed-out gaze with a look of pure unadulterated pleasure in what he was doing to you. Then he pushed his pinky into your ass, his middle and forefingers back into your cunt, all while flicking his tongue over your clit faster than you’d ever imagined possible. A moan tore itself from your throat at the new feeling of him filling your holes and the corners of his eyes crinkled in amusement.

“Fuck, Dean!” You gasped as your extremities began to tingle from the inevitable, oncoming orgasm. His tongue slipped and you tugged his hair back to where you needed him and he groaned, resuming his efforts with renewed determination. “Fuck, I’m gonna come,” you hissed. He slammed his fingers into your holes again and again, even as you tightened around him. Dean’s free hand held your hips down as you came, your entire body shuddering and convulsing with pleasure that seared the edges of your vision and made you momentarily forget your own name.

He gave you a moment to recover as he wiped his mouth on your thigh, gently pulled his hand away, and wiped his fingers off on his own pants.

“You good?” He asked, sounding genuinely concerned but also wrecked with need.

“Take off your fucking pants, Dean,” you panted, sitting up and grabbing for the knotted drawstring before he could move. “Need you to fill me,” you added as you shoved a hand down his pants and closed your fingers around his hot, throbbing cock. “With this.”

“Mmh, wonder how that mouth feels,” Dean muttered as you stroked him, smearing his precum down the shaft.

“Wanna find out?” You offered, tugging his pants down enough to free his erection. It looked much bigger than it felt and your jaw dropped slightly.

“Later,” he hissed. “Not gonna last long,” he grunted when you flicked your tongue over the slit as he quickly shed his tee-shirt.

“How do you want me, Dean?” You pulled away from his cock, the saltiness of him lingering on your tongue. You reached into your nightstand and retrieved a condom, wasting no time in opening it and rolling it onto his length.

“Jesus fuck,” he gritted out and clenched his fists. “Wanna watch you take this cock. Wanted this for so long.” You hurriedly moved so your head was against your pillows, on your back. Dean followed and settled between your thighs, the solidness of his cock pushing gently against your sex. “You want it?” He asked, his eyes darting between yours.

“Fuck me, Dean,” you almost echoed yourself from when you fucked Sam the first time.

With his weight on his elbows, Dean pushed his hips forward slowly and he filled you up, up, up, until he was buried inside of you and you were panting, on the verge of begging for more.

“God, you feel good,” Dean ground out as his hips started to move and his eyes watched your face. You pushed aside the fact Sam said the exact same thing to you that night Dean disappeared. “So fucking good, sweetheart.”

“Dean,” you whined his name and reached down to press on his lower back, encouraging him to fuck you deeper.

“Yeah, baby,” he grunted and got the hint. His hips pushed harder into yours as you tilted up to meet his thrusts. Very aware that it was now sometime around 7:00AM and people were definitely up and about and the doors weren’t exactly built for privacy; you swallowed most of your moans, trying to be quiet without being silent. Dean’s breath was hot on your cheek and neck as he pounded into you. “Feel so good,” he repeated.

“Wanna come on your cock, Dean,” you whispered, unsure if he was into the filthy talk as much as Sam was.

Dean swore under his breath and his hips stuttered and you were almost sure he was going to come right then and there. However, he moved faster, really fucking you into the mattress the way you’d fantasized so many times before.

“Yeah, please,” you gasped. “More, Dean, please!”

He grunted into your neck and then sat back, yanking your ankles over his shoulders. His thrusts went deeper at the new angle and you had to cover your mouth as he rammed into you. His eyes, unfocused and bright green in the dim room, watched your tits bounce with every thrust while the tip of his tongue poked through his teeth, which were slightly bared. He kept his breathing steady and even, hardly making a noise aside from the sound of his hips slamming into the backs of your thighs. A deep moan bubbled up from your belly and you clamped your hands more firmly over your mouth while your eyes rolled back into your head.

“That’s right, sweetheart,” Dean urged. “Let go. Come all over this cock.” He pressed a thumb against your clit once more.

You thought surely you’d died and gone to heaven – or maybe even hell – when your body obeyed yet another Winchester telling you to come on command. A shout was muffled in your hands as pleasure blinded you and made you numb to everything else aside from the rush of adrenaline and hormones that flooded your body. Somewhere in the distance, you heard Dean groan and felt him stop moving before it registered that his lap was now _wet_.

“Sonofabitch,” Dean growled and then resumed fucking you, not giving you anytime to recover. One of hands grabbed your wrists and pinned them next to your head so he could hear all your noises. The other clutched your shins to his chest as he pounded into you.

“Dean, please!” You gasped, unable to form comprehensive thoughts let alone an entire sentence.

“Fuck! Y/N!” He slammed forward, filling you completely with his length, and his eyes squeezed shut as he shuddered and grunted, coming hard while buried inside of you. His orgasm triggered another, smaller one of your own and you shut your eyes tight and bit back a cry so it only came out as a strangled whine. “Shit!” Dean lurched forward at the feeling of you coming yet again, and your legs fell off his shoulders, open to either side as you tried to regain control of your senses.

You weren’t sure how much time had passed when Dean shifted and slowly pulled out of you with a soft groan. He rolled onto his back and took a deep breath as he studied the ceiling in your room. You glanced over at him before fixing your gaze on the ceiling, too.

“So, what now?” You asked, not really expecting an answer.

“Pancakes sound good,” Dean replied, grinning widely. “Maybe a shower, first,” he added after sniffing his armpit. “Definitely a shower, first,” he amended when he sniffed the other one.

You couldn’t help but smile. Dean could go from one extreme to another in half a second and it was part of what you loved so much about him. He leaned over you and placed a soft peck on your cheek before he got out of bed and pulled his sweatpants back on.

“That’s not what I meant,” you said quietly as he pulled his shirt back on, sitting up on your hip to watch him dress.

Dean turned and bent down, placing a long, deep kiss on your lips.

Then a knock came at your door and just as you covered yourself with a pillow and Dean stepped away, Sam’s silhouette filled your door frame.

“Y/N, I’m sorry, I,” he paused when his eyes flicked from Dean to you. “Jesus, it’s about time y’all fucked,” he said, without a trace of irony or jealousy. “Um, meet me in the library when you’re dressed,” he finished and flashed a quick smile.

You and Dean both let go of breaths you hadn’t realized you were holding until the door clicked shut.

“What the actual fuck just happened?” You asked, not expecting Dean to answer.

He just shook his head and sighed. “That’s Sammy for ya. That goddamn sixth sense of his is fucking scary sometimes.” He flashed you a smile and leaned in to kiss your forehead. “See ya in a little bit.” Then Dean, too, left you in your room, bewildered and more confused than ever before.

Was there even a line, anymore?


	3. Chapter Three

**Summary for the Chapter:**

> Final chapter by popular request.

“Who’s hungry?” Dean announced, striding into the library with a stack of pancakes and a few plates. He had syrup tucked under one arm, which Sam deftly caught as soon as it slipped free. Even unrehearsed, these brothers knew each other so damn well and could anticipate the other’s needs. Surely, this breakfast with them would be some sort of farewell meal with no hard feelings, blahblahblah; your heart was steadily sinking into your stomach, leaving no room for breakfast.

The older Winchester set the plates down and started dishing out cakes. Without looking up he asked, “Y/N? Tall or short stack?”

“Um, short, please,” you mumbled. “Maybe just, like, two?”

Dean paused and glanced up at you. “Feelin’ alright, sweetheart?”

“’M fine,” you smiled wanly; you didn’t miss Sam’s look of concern directed at you. Dean handed you the plate with two pancakes on it and you forced a more grateful smile. Not many others were as lucky to receive a homemade breakfast before being sent on their way. “Thanks, they look great.”

“Thanks,” Sam chimed in, taking a plate of four from his brother and smothering them in syrup. Sam rarely ate junk – or sugar – but there were always exceptions.

“Aaand for moi,” Dean grinned, sitting down with his stack of six or seven cakes. “Shit, I forgot the coffee,” he pouted.

“I got it,” you announced, hopping up and darting out of the room before either brother could protest. In truth, you needed a moment to collect yourself before you started bawling in front of them. You braced yourself against the small counter where the coffee maker was and took a few deep, calming breaths. But still the tears stung at your eyes.

“Need some help?” Sam’s voice floated quietly over to you. He didn’t want to startle you.

“I’m good, Sam,” you answered, not lifting your face. Your voice shook and you knew he heard it, but still you poured three cups of coffee.

“What’s wrong?” He asked, closing the distance between you.

“N-nothing,” you lied. “I’m good. Here,” you turned and handed him a mug of coffee. The look of concern on his face was too much and you furiously tried to blink back tears, to no avail. They spilled out onto your cheeks and you glanced away, unable to look at him as your emotions gave you away.

“Hey, hey, hey,” Sam cooed, brushing a tear away with his knuckle. “What’s up? Talk to me.”

“I just,” you paused and took another deep breath to keep your voice from shaking again. “I don’t wanna go, Sam.”

“Go? Where? Why would you – oh, oh, Y/N. You thought we were going to ask you to leave.” It wasn’t a question, yet still you nodded. “Oh my God, no, no,” Sam set the coffee down and took the other mugs from you before he wrapped you in his arms. Despite his words, you started crying uncontrollably into Sam’s chest. Maybe it was because you hadn’t let yourself cry in weeks, despite Dean being gone, or because you were still scared they were going to decide they didn’t need you – or want you – anymore, you weren’t sure. But the waterworks flowed with no signs of letting up. Sam gently smoothed your hair back with one large hand as you clung to him and just let it all out.

“Hey, breakfast’s getting col,” Dean started and immediately shut up once he saw Sam embracing the hot mess that was you. “She okay?” He asked, his voice dropping significantly into the octave he reserved for anger and concern.

You felt Sam shift and knew he was having a conversation with Dean with just his eyes. A deep, shuddering breath drew both their attention back to you, and you slowly disentangled yourself from Sam. “I don’t get it,” you mumbled, feeling helpless. “Why are you both so concerned about me? After what I did,”

“What you did?” Sam interrupted, grinning wryly. “You mean what _we_ did? Y/N, that’s what we were gonna talk about. How to, you know,” he gestured vaguely.

“How it’s gonna be with both of us,” Dean finally said, his voice firm and clear and commanding your attention. The phrase shook you to the core and you felt even more lost than before. Being asked to leave was understandable but being asked to be with both of them…? Your brows knit together in confusion as you looked from one to the other and back again. “C’mon, let’s eat and then figure this shit out, huh?” Dean said, giving you a smarmy little grin. There really was no room for argument.

\--

The plates were stacked up to the side and it was obvious neither brother really knew where to start.

“Mind if I ask a few questions? Just to get started?” You asked.

“Shoot,” Dean said, nodding in your direction.

“H-have you two ever, um, I mean, have y’all ever _shared_ a partner?”

Sam’s eyes darted away from yours when you focused on him, so you looked back to Dean. Dean’s face was slowly reddening and he was staring down at the table, his bottom lip caught between his teeth for a long moment. He finally cleared his throat. “There were some times when we were on the road and, uh, after a bad hunt or even a really good one, Sammy and I would get pretty drunk,” he shrugged one shoulder. “Sometimes, we’d bring someone back with us. To the motel.” He puffed and shook his head. “Took turns.”

The reddening of Sam’s face confirmed Dean’s story. “I mean, we were _really_ wasted. Like, I don’t really remember those nights,” Sam admitted. “Not the whole night, anyway.”

“Yeah,” Dean said, swallowing.

You felt a tinge of arousal at the prospect of being shared or them taking their turns with you. The Winchesters weren’t unattractive men and you’d known them for the better part of two years – which was way better than just one night, in your humble opinion.

“Okay. Should we set boundaries?” You asked, just going off what you’d read or seen online in these situations. “Like, who’s primary and secondary?”

“Hold up,” Dean said and exchanged A Look with Sam. “I uh, I think Sammy and I both consider _you_ our primary,” he said slowly, allowing Sam a nod to confirm. “If that’s okay?”

You mulled it over and it actually took the pressure off you to choose, which was nice. You wondered if Dean did that on purpose. “Yeah, that works,” you agreed. “So, does that mean you’ll be potentially bringing other partners back?”

“I honestly don’t foresee that happening beyond any one-night stands,” Dean said and his honesty kind of shocked you. It was hot to hear him be so open. “And, of course, we’ll clear everything with everyone beforehand,” he added. “But we all know this life isn’t meant for people outside our circle. Bringing others in to this life is just a recipe for disaster,” he lamented, certainly thinking back to his days with Lisa.

You reached across the table and squeezed Dean’s hand gently to let him know you understood. Even when you were on your own, trying to have a ‘normal’ relationship was taxing at best and punishing at worst. There was the constant worry of putting a partner in harm’s way or coming home to find them just gone, unable to handle the lies and untruths anymore.

“I agree,” Sam said.

“Same,” you replied, finding a mild bit of relief that you were all on the same page. “So, my next question,” you hesitated, feeling your face redden at the thought. “What if, um, what if I want both of you? Together?”

The silence was long and agonizing and you were almost certain they were going to draw the line.

“I think that’s something Dean and I will have to work out,” Sam finally said. It looked like he was rolling the words around in his mouth, tasting each one before it formed on his tongue.

“It’s not off the table,” Dean said, lowly. You looked at him and found his gaze dark, locked on you, and suddenly you felt naked. Your skin got warm all over and your breath hitched in your throat – Dean was game to take you at the same time as his brother. “Is that something you want?” His voice was heavier, thicker, mesmerizing.

“I, I’m not opposed to it,” you mumbled, unable to retain eye contact with the older Winchester any longer.

“You thought about Sammy and me taking you? Together?” Dean stood up and walked around the table to stand directly behind you, his hands heavy on your shoulders. The only other time you’d ever felt this small near Dean was when he was mad. You believed his question to be rhetorical, so you just shrugged a shoulder as if to say, _who hasn’t?_ “Answer me, sweetheart,” Dean rumbled, leaning down to put his lips close to your ear.

“I, I,” your eyes lifted to Sam, first. He was seated, still, leaning back in his chair with one fist under his chin, his index finger pointing straight up along his cheek, and his gaze was also darkened and intense. “M-maybe, like once or twice?” You tried, almost scared to look at Dean with how much heat he was putting off just staring at you.

“Once or twice?” Sam asked; his voice was lowered, too. “Y’know you’re about as terrible a liar as Dean, Y/N,” he added when you nodded. “So how many times?”

“I, I don’t know,” you admitted, staring down at the table. “A lot.”

Dean tsked into your ear and it gave you goose pimples so fast that it almost hurt. Your nipples hardened under your lightly-padded bra and you instinctively tilted your head away. A large, warm hand gripped your jaw, stopping your movement, and then Dean’s soft, plush lips were against yours. His tongue licked your bottom lip before sliding between them. You moaned shamelessly into his mouth, reaching up to grasp the back of his head. This kiss was meant to work you up, to tease you mercilessly, to make you want more.

Sam cleared his throat after several moments and you made to pull away, but Dean didn’t let you escape that easily. He pulled you back to him greedily and you whimpered, turned on more than you had ever thought possible. It was almost as if Dean were challenging Sam to do something about his monopoly on your attention.

“Guys,” Sam tried and you could barely even glance in his direction before Dean moved your chin and Sam was out of your peripheral. “Guys!” He tried again.

“Sam, shut up or get in on this,” Dean finally growled and it sent a wave of heat directly to your sex. He yanked your chair out from the table and pulled you to your feet, covering your mouth with his before you could even get a coherent thought formed. You pressed your body against Dean’s, loving the way he was solidly built and felt against you, then he reached down and grabbed your ass before giving it a good smack. You yelped in surprise but couldn’t pull away because there was a warm presence at your back and it smelled like Sam Winchester. His large hands gripped your hips and pulled them back against him. You moaned into Dean’s mouth and then one of Sam’s hands slid around your front and cupped your sex.

“I was gonna say, let’s move this somewhere else,” Sam explained and Dean slowly pulled away from you. “My room’s closest.”

Suddenly, you felt dizzy with the prospect of being with the Winchesters – both of them – at the same time. “Gimme a minute. ’M not sure my legs work,” you slurred.

Then Dean bent down and slung you over his shoulder with sickening ease. The bunker flashed by in snippets because you were so focused on the fact you were being carried to a bedroom to be had by _both_ Winchesters. Dean unceremoniously tossed you onto the bed and you sat back against Sam’s pillows, your eyes darting from one brother to the other. Sam kicked his door shut and pulled his plaid shirt off in one smooth motion; Dean followed suit with his own plaid shirt.

Breathlessly, you watched as each one pulled their tee shirts off next. It wasn’t like you hadn’t seen either one of them naked before – you had – but never together. It was overwhelming.

“Guys, wait,” you blurted out and both of them stopped moving, their focus locked only on you. “I, I think we should maybe take some time? Think all of this over? I mean, just in case somebody has second thoughts.”

Dean’s countenance lengthened as he frowned softly. “You alright, baby?”

“I’m fine, really, I’m actually _insanely_ turned on by the idea of you guys, um, together, but,”

“It just feels too quick?” Sam tried, putting his hands on his hips in his classic I’m Uncomfortable stance.

“Kinda,” you said, shrugging and pulling your knees up to your chin.

“Well, what am I supposed to do with this?” Dean complained, gesturing to the bulge in his jeans. You bit back a smirk as Sam rolled his eyes.

One Week Later

You were starting to think this whole group sex thing was never going to happen. Sam and Dean seemed to be tip-toeing around the topic and despite the motel only having a single king bed left when you rolled into town, neither one of them did more than kiss you just a little bit before going to sleep each night. You were frustrated and burning with desire, wondering how you were supposed to spend one more night between the Winchesters without either one of them touching you. Lying awake, you stared up at the ceiling, getting angrier and angrier at both of them. If they didn’t want this, then what the fuck were you doing wasting everyone’s time?

As if he could sense your aggravation, Dean suddenly pulled you against him. You’d discovered that he was prone to sleep-grabbing after the first night in the motel. So, you didn’t think much of it until his lips started placing feather-light kisses on your shoulder and neck. “You awake?” He whispered, his voice deep and thick with want.

“Yeah,” you whispered back, nodding.

Dean’s hand slid down to your hip and he pushed the bottom hem of your sleep shorts up onto your ass. “Wanna fool around?” His lips found your jaw and you nodded. He wasted no time in slipping his hand into your shorts, finding you without underwear. He groaned softly and began brushing his fingertips against your sex, teasing you and working you up. Except that you were so pent up, it didn’t take much before the floodgates opened. At the first sign of wetness, Dean swept his index finger through your folds and smeared it up to your clit.

It felt so good and you sighed quietly, listening for Sam’s breathing to become quicker or shallower. Dean didn’t make you wait before he really got to work, his finger rubbing and circling your clit – the only goal: to make you come. You gasped when he sank a finger into you to collect more slick and then his other hand was clamped over your mouth. A couple minutes later, you were trembling and shaking with a long-overdue climax, whimpering softly into Dean’s hand that still covered your mouth.

“Fuck that was hot, baby,” he whispered into your ear and you felt him shift behind you as his hand departed from between your legs and tugged your shorts down past your ass. “Wanna fuck you so bad.”

Sam cleared his throat and you froze, having no idea when he’d woken up. “I like it better when she screams,” he said casually and a flood of fire filled your belly. Then he rolled over to face you and Dean pulled his hand from your mouth. “But the sounds you make when you’re trying to be quiet are fucking hot, too,” he smiled and kissed your lips softly. “Made me so hard,” he muttered, gently nipping your bottom lip.

“Sam,” you breathed, reaching up to brush his hair out of his face. “Sam, I didn’t know you were awake.”

“I know,” he grinned wider and slipped a hand between your legs, making you gasp. “Fuck, you’re so wet. Dean get you all worked up?”

You couldn’t form words, so you just nodded slowly.

“You want him to fuck you?” Sam asked, his voice obtaining a bit of darkness to it that was new to you.

“Y-yeah,” you affirmed.

Sam shoved two thick fingers up into your cunt and you gasped, arching against Dean. Dean, who’d been silent and still behind you, as if waiting to see how all of this unfolded, began rutting his cock against your ass. “Want Dean to fill you just like this?” Sam rumbled.

“Yes,” you moaned, reaching down and grabbing Sam’s cock over his sweatpants. It was hard and warm to the touch and made you realize how much you missed it.

“And what should we do with that?” He grinned, loving the look of utter need on your face. “Think she should suck me off, Dean?”

“If it makes you happy and shuts you up,” Dean fired back, grinding his hips against your ass even harder. “Wanna stuff her full of this cock,” he groaned, yanking your shorts the rest of the way off, and you shuddered.

Sam withdrew his fingers and held them against your lips. You opened for him, licking his fingers clean as Dean grabbed your thigh and hooked it over his hip, then lined himself up at your entrance. “That’s so fucking hot, Y/N,” Sam murmured, pushing the blankets back a bit just as Dean sank into your wet warmth. “Fuck.” He covered your hand on his cock with his free hand, making you grip it tighter.

Dean held your hip tightly as he pounded into you, forcing small gasps and moans from you as Sam pushed his sweatpants down enough to free his cock. Once he’d done that, he grabbed you and started jerking off, using your hand to do it.

“You feel so good, sweetheart,” Dean muttered into your ear just before his teeth nipped your lobe. “God, I want this pussy every fucking night.”

“Oh, God, Dean,” you moaned, almost unable to handle the filth coming out of his mouth.

“Looks like you’re gonna be sore,” Sam smirked. “Cause when he’s done with you? It’s my turn.”

All you knew how to do in response was moan and it seemed to encourage them, because Dean started fucking you even harder. Sam’s gaze fell to your breasts, bouncing within the confines of an over-sized tee that probably once belonged to him. Dean’s free hand groped at your chest, tweaking your nipple through the fabric and making your moans get higher in pitch.

“Wanna fuck those tits,” he muttered, seemingly to himself. But Dean was on it and held you against his chest as he rolled onto his back with yours flush against his chest, fucking up into you with every ounce of force he had in his hips. Sam moved quickly, shoving the shirt over your breasts and head and yanking it off your arms. You arched as Sam knelt on either side of you, lowering his cock to your chest, and then you pushed your breasts together for him. “Good girl,” he sighed as he slid his length between your breasts. “Now spit.”

You tilted your chin down and spit on the tip of his cock as Sam moved slowly back and forth.

Underneath you, Dean groaned and slammed into you, panting heavily. It wouldn’t be long before he came and your pussy clenched at the thought of making him come. “Shit!” Dean groaned, his fingers digging into your hips.

“Again,” Sam ordered when the spit was dried up. You spat on his cock again, barely able to focus on anything besides how good it felt to have Dean splitting you open. Suddenly, a rough fingertip found your clit and started rubbing again.

“Oh, oh God,” you panted, unsure if you could handle coming again so soon. The pressure was light and the pace was fast and combined with Sam fucking your tits while Dean fucked your cunt, it didn’t take long at all before you were coming yet again. This time, you didn’t try to stay quiet and the motel room was filled with your sounds of pleasure. “Dean! FUCK!” Your entire body trembled with the force of your climax.

“Fuck, Y/N!” Dean grunted and quickly pulled out, following you headlong into orgasmic bliss. He coated your inner thighs as he shuddered under you.

“My turn,” was all Sam said before he rolled onto his back and dragged you off Dean. You moved so quickly that you barely had your knees on either side of his hips when Sam rammed his cock into your still-pulsing warmth.

“SAM!” You wailed, clutching onto his shoulders as he got into a brutally fast pace. Your main thought was that you were glad you were going to be able to lay down in the car on the way home tomorrow. It was all you could do to stay upright as Sam pounded into you.

“Come for me, Y/N,” he panted, staring up at your face as you keened.

“I, fuck! I can’t!” You shook your head; two intense orgasms were enough and you doubted if you could handle another one.

“Dean,”

“On it,” rasped the older Winchester as he sat up and moved behind you.

“Dean, please, no,” you whined, half-heartedly pushing his hands away from you as they came around your front.

“It’s okay, baby,” he whispered into your ear. Having him at your back, with his broad warmth and low voice, while his little brother fucked you silly was so toe-curlingly comforting that you knew you were done for, anyway. “Can we make you feel good?”

You nodded; there was no point in trying to fight it and _god_ you wanted to come again for them. Then Dean’s presence at your back lessened and Sam’s thrusts slowed. The younger Winchester wrapped his arms around your waist and sat up suddenly, taking you with him as he smoothly laid you back, onto Dean’s chest, and hooked your ankles over his own shoulders. Dean wrapped one arm around you, pinning your arms at your sides, and with his free hand, he started playing with your breasts and nipples. Sam lowered a hand between your legs and you keened when his middle finger found your swollen nub.

“God, you’re so tight, Y/N,” Sam groaned, already ramming into you once more. “Gonna come for me?”

“Be a good girl and come for Sam,” Dean rumbled in your ear while he lightly slapped the side of your breast and your eyes squeezed shut once more. Of all the things you never thought you’d hear Dean say, that had to rank in the top five.

“Fuck, God, Sam!” You moaned, like before.

“Yeah, baby,” he muttered back, along with some other things, but all you could hear was white noise as your orgasm ripped through you and made you _wail_. You lost feeling in your entire body as it quaked in Dean’s arms from your fingertips to your toes and everywhere in between. Your cunt clenched down on Sam’s cock so tightly that it was forced out and he shoved it back in, making you scream. If Dean’s arm hadn’t been wrapped around you, you were sure your back would’ve arched hard enough to nearly snap in half. Sam finally pulled out and came all over your lower abdomen with a shout, which surprised you because you thought he came between your legs with how wet it had become there.

Dean’s arm released and he was gently soothing the slap marks he’d left on your breasts while you caught your breath and returned to your body.

“Holy. Shit.” Those were the only two words you could manage.

“She’s a squirter,” Sam panted, gently easing your still-trembling legs down from his shoulders.

“No shit,” Dean smirked.

“No shit?” You parroted, huffing a laugh. “Jesus Christ.”

“Well, that was fun,” Dean said and shifted behind you. “I’m beat.”

“I think I need a shower?” You said, still too dazed to move; the guys moved around you, instead. “But I’m not sure my legs work.”

“C’mon, I’ll get it started for you,” Sam huffed and helped you sit up. Dean went around and gathered your sleeping clothes, then handed them to you even as he pulled his own sweatpants back on. A couple minutes later, Sam emerged still fully nude and Dean groaned, turning his back. Sam just smirked and shook his head. “Should be warm enough, c’mon,” he said and you stood up with his assistance.

“Thanks Sam,” you yawned. “I’ll take it from here,” you grinned at him as you entered the bathroom, moving to shut the door on him.

He pouted a little bit. “You don’t want any, uh, help?”

“Sam, if you touch me again tonight, I’ll need a wheelchair to get me to the car in the morning,” you joked.

He grinned, tilted his head down, and nodded. “Fair enough.”

You shut the door and leaned against it for a long moment, holding the heels of your palms against your eyes. _Did that really just happen? How did this become my life?_ A slow smile spread across your face and you dropped your hands and tilted your head back, giggling under your breath.

And as for that line?

Well, it might as well never have existed to begin with.

**Notes for the Chapter:**

> the end! thanks for reading and leaving feedback, y'all are great.


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